Bromine → 1-(4-Bromo-3-methylphenyl)piperazine hydrochloride

HRID 1371994

Reaktionsgleichung

Reaktionsgleichung von HRID 1371994
[ClH:1].Cl.[CH3:3][C:4]1[CH:5]=[C:6]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:7]=[CH:8][CH:9]=1.[Br:16]Br>C(O)(=O)C.O>[ClH:1].[Br:16][C:9]1[CH:8]=[CH:7][C:6]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:5][C:4]=1[CH3:3]

Komponenten

5

Edukt 2

HCID 24408BromineHCID 831101-(m-Tolyl)piperazine dihydrochloride

Produkt 1

HCID 210710171-(4-Bromo-3-methylphenyl)piperazine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 966 mg (4.0 mmol) of 1-(3-Methylphenyl)piperazine dihydrochloride in 9 mL of acetic acid and 1 mL of water at 0° C. was added 640 mg (4.0 mmol) of bromine. After 1 hour, the reaction was concentrated to an oil in vacuo, and the oil was partitioned between ethyl acetate and 1M NaOH. The phases were separated, and the ethyl acetate phase was washed once each with water and brine, dried over Na2SO4, filtered, and the filtrate was concentrated to an oil in vacuo. The oil was dissolved in a minimum volume of methanol, and the solution was acidified with 2M HCl in ether. The product was isolated by filtration. 1H NMR (D2O, 400 MHz) 7.37 (d, 1H), 6.85 (s, 1H), 6.76 (d, 1H), 3.37 (m, 8H), 2.17 (s, 3H) ppm.

Aufarbeitung

  1. concentrationthe reaction was concentrated to an oil in vacuo
  2. customthe oil was partitioned between ethyl acetate and 1M NaOH
  3. customThe phases were separated
  4. washthe ethyl acetate phase was washed once each with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated to an oil in vacuo
  8. dissolutionThe oil was dissolved in a minimum volume of methanol
  9. customThe product was isolated by filtration

Quellen und Nachweise

ORD-Eintrag
ord-25113aa914db4229ae8967981cf18283
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157464B2

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